They've also said that you'll need to show something to prove that you've had at least one 2+ day guest stay in the last 6 months (to be grandfathered in), and recently have assured that your permit will be transferable should you sell the home.

Look for CPAs who stay abreast of evolving tax codes related to real estate and possess a comprehensive understanding of deductions, credits, and depreciation strategies unique to the industry. 

The baked in assumption to "continued cash flow" is that you stay profitable.

And while yes, no one has the same pricing (combination of factors), I also continue to check on a regular basis our rankings and how we "present" on total costs per stay vs. our competitors.My gut says there is price creep and we might have a ways to go before the market really corrects.

As far as benefit to the seller goes, @Matthew Paul I think you are probably right on the money and regardless of whether they would have preferred to stay in this house rather than move, it is likely providing them some excellent cash flow; and I'd be hard-pressed to come up with a deal that serves both parties better than the current situation. 

Personally, I airbnb half of my house, individual rooms, and stay nearly 100% booked.

The substitute of collateral was more of a scenario where you sold for $155K, and instead of paying off the $88K loan in your scenario, those funds stayed at the title company and were used on a cash purchase happening nearby in date. 

Attend events regularly, stay engaged in conversations, and keep learning through books and podcasts.

She can use that money to get a hotel room or short term rental....or stay with family or friends.

Would appreciate honest feedback for the best way to get and stay organized!